Phthalic acid diamide, method for the production thereof and the use of the same as a pesticide

ABSTRACT

Novel phthalamides of the formula (I)  
                 
 
     in which  
     X, Y, n, m, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, a, b and c have the meanings given in the description,  
     a process for preparing these compounds and their use for controlling pests.

[0001] The present invention relates to novel phthalamides, to a processfor the preparation and to their use as pesticides.

[0002] It is already known that numerous phthalamides have insecticidalproperties (cf. EP 0 919 542 A and EP 1 006 107 A). However, withrespect to their compatibility with plants and efficacy, the knowncompounds are not always satisfactory. It has now been found thatphthalamides which contain a silicon atom in the side chain have verygood insecticidal and acaricidal properties and are tolerated well byplants.

[0003] This invention, accordingly, provides phthalamides of the formula(I)

[0004] in which

[0005] X and Y independently of one another represent hydrogen, halogen,cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cycloalkyl,halogenocycloalkyl, cycloalkyloxy, halogenocycloalkyloxy,—S(O)_(d)-alkyl, —S(O)_(d)-halogenoalkyl or represent in each caseoptionally substituted phenyl, phenoxy, heteroaryl or heteroaryloxy,

[0006] n represents 1, 2, 3 or 4,

[0007] m represents 1, 2, 3, 4 or 5,

[0008] R¹, R², R³ and R⁴ independently of one another representhydrogen, alkyl, halogenoalkyl or cycloalkyl,

[0009] R⁵, R⁶ and R⁷ independently of one another represent alkyl oralkoxy,

[0010] A represents —S(O)_(d)— or oxygen,

[0011] a represents 1, 2, 3 or 4, with the proviso that the repeat unit—CR¹R²— may have identical or different meanings if a represents 2, 3 or4,

[0012] b represents 0 or 1,

[0013] c represents 0, 1, 2, 3 or 4, with the proviso that the repeatunit —CR³R⁴— may have identical or different meanings if c represents 2,3 or 4,

[0014] d represents 0, 1 or 2.

[0015] Depending on the nature and number of substituents, the compoundsof the formula (I) may, if appropriate, be present as geometrical and/oroptical isomers, regioisomers and/or configurational isomers or isomermixtures thereof of varying compositions. What is claimed by theinvention are both the pure isomers and the isomer mixtures.

[0016] Furthermore, it has been found that the novel compounds of theformula (I) obtained by reacting imides of the formula (II)

[0017] in which

[0018] X, Y, n and m have the meanings given above

[0019] with silylamines of the formula (III)

H₂N—(CR¹R²)_(a)-A_(b)-(CR³R⁴)_(c)—Si(R⁵R⁶R⁷)  (III)

[0020]  in which

[0021] R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A, a, b and c have the meanings givenabove,

[0022]  if appropriate in the presence of a diluent.

[0023] Finally, it has been found that the compounds of the formula (I)according to the invention have very good insecticidal properties andcan be used in both crop protection and in the protection of materialsfor controlling undesirable pests, such as insects and acarids.Surprisingly, the phthalamides according to the invention, which containa silicon atom in the side chain, have very good insecticidal-andacaricidal activity and are at the same time tolerated well by plants.

[0024] The formula (I) provides a general definition of the phthalamidesaccording to the invention.

[0025] X and Y independently of one another preferably representhydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl,C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogenocycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-halogenocycloalkyloxy, —S(O)_(d)—C₁-C₆-alkyl,—S(O)_(d)—C₁-C₆-halogenoalkyl or represent phenyl, phenoxy, heteroarylor heteroaryloxy, each of which is optionally mono- to tetrasubstitutedby identical or different substituents from the group consisting ofhalogen, C₁-C₆-alkyl and C₁-C₆-halogenoalkyl.

[0026] X and Y furthermore independently of one another preferablyrepresent phenyl, phenoxy, heteroaryl or heteroaryloxy, each of which isoptionally mono- to tetrasubstituted by identical or differentsubstituents from the group consisting of C₁-C₆-alkoxy,C₁-C₆-halogenoalkoxy, C₁-C₆-alkylthio and C₁-C₆-halogenoalkylthio.

[0027] n preferably represents 1, 2 or 3.

[0028] m preferably represents 1, 2, 3 or 4.

[0029] R¹, R², R³ and R⁴ independently of one another preferablyrepresent hydrogen, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl orC₃-C₆-cycloalkyl.

[0030] R⁵, R⁶ and R⁷ independently of one another preferably representC₁-C₆-alkyl or C₁-C₆-alkoxy.

[0031] A preferably represents —S(O)_(d)— or oxygen.

[0032] a preferably represents 1, 2, 3 or 4, with the proviso, that therepeat unit —CR¹R²— may have identical or different meanings if arepresents 2, 3 or 4.

[0033] b preferably represents 0 or 1.

[0034] c preferably represents 0, 1, 2, 3 or 4, with the proviso thatthe repeat unit —CR³R⁴— may have identical or different meanings if crepresents 2, 3 or 4.

[0035] d preferably represents 0, 1 or 2.

[0036] X and Y independently of one another particularly preferablyrepresents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 9 fluorine, chlorine and/orbromine atoms, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 9fluorine, chlorine and/or bromine atoms, C₃-C₆-cycloalkyl,—S(O)_(d)—C₁-C₄-alkyl, —S(O)_(d)—C₁-C₄-halogenoalkyl having 1 to 9fluorine, chlorine and/or bromine atoms.

[0037] Y furthermore particularly preferably represents phenyl, phenoxy,5- or 6-membered heteroaryl or heteroaryloxy having 1 to 4 heteroatomsincluding 0 to 4 nitrogen atoms, 0 to 2 nonadjacent oxygen atoms and/or0 to 2 nonadjacent sulphur atoms (in particular furyl, furyloxy,thienyl, thienyloxy, pyrrolyl, pyrrolyloxy, tetrazolyl, pyridyl,pyridyloxy, pyrimidinyl, pyrimidinyloxy, pyridazinyl, pyridazinyloxy,pyrazinyl, pyrazinyloxy), each of which is optionally mono- totetrasubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, bromine, iodine, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl having 1 to 9 fluorine, chlorine and/or bromineatoms, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 9 fluorine,chlorine and/or bromine atoms, C₁-C₄-alkylthio, C₁-C₄-halogenoalkylthiohaving 1 to 9 fluorine, chlorine and/or bromine atoms.

[0038] n particularly preferably represents 1 or 2.

[0039] m particularly preferably represents 1, 2 or 3.

[0040] R¹, R², R³ and R⁴ independently of one another particularlypreferably represents hydrogen, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having1 to 9 fluorine, chlorine and/or bromine atoms or C₃-C₆-cycloalkyl.

[0041] R⁵, R⁶ and R⁷ independently of one another particularlypreferably represents C₁-C₃-alkyl or C₁-C₃-alkoxy.

[0042] A particularly preferably represents —S(O)_(d)— or oxygen.

[0043] a particularly preferably represents 1, 2 or 3, with the provisothat the repeat unit —CR¹R²— may have identical or different meanings ifa represents 2 or 3.

[0044] b particularly preferably represents 0 or 1.

[0045] c particularly preferably represents 0, 1, 2 or 3, with theproviso that the repeat unit —CR³R⁴— may have identical or differentmeanings if c represents 2 or 3.

[0046] d particularly preferably represents 0, 1 or 2.

[0047] X very particularly preferably represents chlorine, bromine,iodine.

[0048] Y very particularly preferably represents methyl, ethyl,n-propyl, isopropyl, trifluoromethyl, pentafluoroethyl,n-heptafluoropropyl, isoheptafluoropropyl, trifluoromethoxy or—OCF₂CF₂H.

[0049] Y furthermore very particularly preferably represents phenoxy,pyridinyloxy or tetrazolyl, each of which is mono- to trisubstituted byidentical or different substituents from the group consisting offluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl, —CF₃, —CHF₂, —CClF₂,—CF₂CHFCl, —CF₂CH₂F, —CF₂CCl₃, —CH₂CF₃, —CF₂CHFCF₃, —CH₂CF₂H,—CH₂CF₂CF₃, —CF₂CF₂H, —CF₂CHFCF₃, —OCF₃, —OCHF₂, —OCF₂CF₂H, —SCF₃,—SCHF₂.

[0050] n very particularly preferably represents 1.

[0051] m very particularly preferably represents 2.

[0052] R¹, R², R³ and R⁴ independently of one another very particularlypreferably represent hydrogen, methyl or ethyl.

[0053] R⁵, R⁶ and R⁷ independently of one another very particularlypreferably represents methyl, ethyl, methoxy or ethoxy.

[0054] A very particularly preferably represents —S(O)_(d)— or oxygen.

[0055] a very particularly preferably represents 1, 2 or 3, with theproviso that the repeat unit —CR¹R²— may have identical or differentmeanings if a represents 2 or 3.

[0056] b very particularly preferably represents 0 or 1.

[0057] c very particularly preferably represents 0, 1 or 2, with theproviso that the repeat unit —CR³R⁴— may have identical or differentmeanings if c represents 2.

[0058] d very particularly preferably represents 0, 1 or 2.

[0059] Very particular preference is furthermore given to compounds ofthe formula (I-a)

[0060] in which

[0061] Y¹ and Y² independently of one another have the meanings of theradical Y given above,

[0062] A represents sulphur or oxygen,

[0063] b represents 0 or 1 and

[0064] X, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, a and c have the meanings givenabove.

[0065] Very particular preference is furthermore given to compounds ofthe formula (I-b)

[0066] in which

[0067] Y¹ and Y² independently of one another have the meanings of theradical Y given above,

[0068] A represents sulphur or oxygen,

[0069] b represents 0 or 1 and

[0070] X, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, a and c have the meanings givenabove.

[0071] Very particular preference is furthermore given to compounds ofthe formulae (I-a) and the formula (I-b), in which

[0072] A represents SO or SO₂.

[0073] Very particular preference is furthermore given to compounds ofthe formulae (I-a) and the formula (I-b), in which

[0074] Y¹ and Y² independently of one another have the preferred,particularly preferred or very particularly preferred meanings of theradical Y given above,

[0075] A represents S(O)_(d) or oxygen,

[0076] b represents 0 or 1,

[0077] d represents 0, 1 or 2 and

[0078] X, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, a and c have the preferred,particularly preferred or very particularly preferred meanings givenabove.

[0079] Preference is furthermore given to compounds of the formula (I)in which R⁵, R⁶ and R⁷ each represent methyl.

[0080] Preference is furthermore given to compounds of the formula (I)in which A represents S, SO or SO₂.

[0081] Preference is furthermore given to compounds of the formulae(I-a) and the formula (I-b) in which Y¹ represents C₁-C₄-alkyl,preferably trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl,isoheptafluoropropyl, particularly preferably isoheptafluoropropyl.

[0082] Preference is furthermore given to compounds of the formulae(I-a) and the formula (I-b) in which Y² represents methyl.

[0083] Saturated hydrocarbon radicals, such as alkyl, can in each casebe straight-chain or branched as far as this is possible, including incombination with heteroatoms, such as, for example, alkoxy.

[0084] However, the general or preferred radical definitions orillustrations given above can also be combined with one another asdesired, i.e. between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to the precursorsand intermediates.

[0085] Using4-chloro-2-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-isoindole-1,3(2H)-dioneand 1-{[(trimethylsilyl)methyl]sulphanyl}-2-propanamine as startingmaterials, the cause of the process according to the invention can beillustrated by the equation below.

[0086] The formula (II) provides a general definition of the imidesrequired as starting materials for carrying out the process according tothe invention. In this formula, X, Y, n and m preferably, particularlypreferably and very particularly preferably have those meanings whichhave already been mentioned in connection with the description of thecompounds of the formula (I) according to the invention as beingpreferred, particularly preferred, etc., for these radicals.

[0087] Imides of the formula (II) are known (cf. EP 0 919 542 A and EP 1006 107 A).

[0088] The formula (III) provides a general definition of thesilylamines required as starting materials for carrying out the processaccording to the invention. In this formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷,A, a, b and c preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, particularly preferred,etc., for these radicals.

[0089] Some of the silylamines of the formula (III) are known (cf.Tetrahedron Lett. 1999, 40, 4467).

[0090] Silylamines of the formula (III-a)

H₂N—(CR¹R²)_(a)—S—(CR³R⁴)_(c)—Si(R⁵R⁶R⁷)  (III-a)

[0091] in which

[0092] R¹, R², R³, R⁴, R⁵, R⁶, R⁷, a and c have the meanings givenabove,

[0093] can be prepared, for example, by reacting

[0094] aziridines of the formula (IV)

[0095]  in which

[0096] R¹ and R² have the meanings given above

[0097] with thiols of the formula (V)

HS—(CR³R⁴)_(c)—Si(R⁵R⁶R⁷)  (V)

[0098]  in which

[0099] R³, R⁴, R⁵, R⁶, R⁷ and c have the meanings given above,

[0100] if appropriate in the presence of a diluent (for example,methanol) (cf. J. Org. Chem. 1963, 28, 1496).

[0101] Suitable diluents for carrying out the process according to theinvention are in each case all customary inert organic solvents.Preference is given to using optionally halogenated aliphatic, alicyclicor aromatic hydrocarbons, such as petroleum ether, hexane, heptane,cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin;chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbontetrachloride, dichloroethane or trichloroethane; ethers, such asdiethyl ether, diisopropyl ether, methyl tert-butyl ether, methyltert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,1,2-diethoxyethane or anisole; nitriles, such as acetonitrile,propionitrile, n- or isobutyronitrile or benzonitrile; amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide; esters, such asmethyl acetate or ethyl acetate; sulphoxides, such as dimethylsulphoxide; or sulphones, such as sulpholane; carboxylic acids, such asformic acid or acetic acid. Particularly preferably, the process iscarried out in acetic acid or in the absence of a diluent.

[0102] When carrying out the process according to the invention, thereaction temperatures can in each case be varied within a relativelywide range. In general, the process is carried out at temperaturesbetween 20° C. and 150° C., preferably between 50° C. and 120° C.

[0103] When carrying out the process according to the invention, ingeneral from 1 to 3 mol of a compound of the formula (III) are employedper mole of the compound of the formula (II). However, it is alsopossible to employ the reaction components in other ratios. Work-up iscarried out by customary methods. In general, the reaction mixture isconcentrated, the residue is taken up in a suitable solvent and theproduct is freed of any impurities that may still be present bychromatography.

[0104] All processes according to the invention are generally carriedout under atmospheric pressure. However, in each case it is alsopossible to operate under elevated or reduced pressure.

[0105] The active compounds according to the invention are suitable forcontrolling animal pests, in particular insects, arachnids andnematodes, which are encountered in agriculture, in forestry, in theprotection of stored products and of materials, and in the hygienesector, and are well tolerated by plants and have favourable toxicity towarm-blooded animals. They may be preferably employed as plantprotection agents. They are active against normally sensitive andresistant species and against all or some stages of development. Theabovementioned pests include:

[0106] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

[0107] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0108] From the order of the Chilopoda, for example, Geophiluscarpophagus and Scutigera spp.

[0109] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0110] From the order of the Thysanura, for example, Lepisma saccharina.

[0111] From the order of the Collembola, for example, Onychiurusarmatus.

[0112] From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

[0113] From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

[0114] From the order of the Dermaptera, for example, Forficulaauricularia.

[0115] From the order of the Isoptera, for example, Reticulitermes spp.

[0116] From the order of the Phthiraptera, for example, Pediculushumanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp.and Damalinia spp.

[0117] From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

[0118] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

[0119] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp. and Psylla spp.

[0120] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

[0121] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon soistitialis, Costelytra zealandica and Lissorhoptrusoryzophilus.

[0122] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.

[0123] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

[0124] From the order of the Siphonaptera, for example, Xenopsyllacheopis and Ceratophyllus spp.

[0125] From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

[0126] The phytoparasitic nematodes include, for example, Pratylenchusspp., Radopholus sirmilis, Ditylenchus dipsaci, Tylenchulussemipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp.,Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.,Bursaphelenchus spp.

[0127] In particular, the compounds of the formula (I) according to theinvention have excellent activity against caterpillars, beetle larvae,spider mites, aphids and leaf-mining flies.

[0128] If appropriate, the compounds according to the invention can, atcertain concentrations or application rates, also be used as herbicidesor microbicides, for example as fungicides, antimycotics andbactericides. If appropriate, they can also be employed as intermediatesor precursors for the synthesis of other active compounds.

[0129] All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and including the plant cultivars protectable or not protectableby plant breeders' rights. Plant parts are to be understood as meaningall parts and organs of plants above and below the ground, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds,roots, tubers and rhizomes. The plant parts also include harvestedmaterial, and vegetative and generative propagation material, forexample cuttings, tubers, rhizomes, offsets and seeds.

[0130] Treatment according to the invention of the plants and plantparts with the active compounds is carried out directly or by allowingthe compounds to act on their surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

[0131] The active compounds according to the invention can be convertedinto the customary formulations, such as solutions, emulsions, wettablepowders, suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound and microencapsulations in polymericsubstances.

[0132] These formulations are produced in a known manner, for example bymixing the active compounds according to the invention with extenders,that is liquid solvents and/or solid carriers, optionally with the useof surfactants, that is emulsifiers and/or dispersants and/orfoam-formers.

[0133] If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, and also water.

[0134] Suitable solid carriers are:

[0135] for example, ammonium salts and ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals, such as highlydisperse silica, alumina and silicates; suitable solid carriers forgranules are: for example, crushed and fractionated natural rocks suchas calcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;

[0136] suitable emulsifiers and/or foam-formers are: for example,nonionic and anionic emulsifiers, such as polyoxyethylene fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates;

[0137] suitable dispersants are: for example, lignosulphite wasteliquors and methylcellulose.

[0138] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

[0139] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organicdyestuffs, such as alizarin dyestuffs, azo dyestuffs and metalphthalocyanine dyestuffs, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0140] The formulations generally comprise between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%.

[0141] The active compound according to the invention can be used incommercially available formulations and in the use forms prepared fromthese formulations as a mixture with other active compounds which arealso known, such as insecticides, attractants, sterilizing agents,bactericides, acaricides, nematicides, fungicides, growth-regulatingsubstances or herbicides. The insecticides include, for example,phosphoric acid esters, carbamates, carboxylates, chlorinatedhydrocarbons, phenylureas and substances produced by microorganisms,inter alia.

[0142] Particularly suitable co-components are, for example, thefollowing compounds:

[0143] Fungicides:

[0144] aldimorph, ampropylfos, ampropylfos-potassium, andoprim,anilazine, azaconazole, azoxystrobin,

[0145] benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

[0146] calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0147] debacarb, dichlorophen, diclobutrazole, diclofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine,dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0148] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

[0149] famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulphamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox, guazatine, hexachlorobenzene,hexaconazole, hymexazole,

[0150] imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

[0151] kasugamycin, kresoxim-methyl, copper preparations, such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0152] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0153] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0154] ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,oxyfenthiin,

[0155] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,procymidone, propamocarb, propanosine-sodium, propiconazole, propineb,pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

[0156] quinconazole, quintozene (PCNB),

[0157] sulphur and sulphur preparations,

[0158] tebuconazole, tecloftalam, tecnazene, tetcyclasis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,triflumizole, triforine, triticonazole,

[0159] uniconazole,

[0160] validamycin A, vinclozolin, viniconazole,

[0161] zarilamide, zineb, ziram and also

[0162] Dagger G, OK-8705, OK-8801,

[0163]α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0164]α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

[0165]α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

[0166]α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0167](5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,

[0168] (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0169]1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

[0170]1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone-O-(phenylmethyl)-oxime,

[0171] 1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

[0172] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

[0173] 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

[0174]1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

[0175]1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

[0176]1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0177] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0178]2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

[0179]2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,

[0180] 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

[0181] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0182] 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

[0183] 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

[0184]2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,

[0185]2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

[0186] 2-aminobutane,

[0187] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0188]2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

[0189]2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0190] 2-phenylphenol (OPP),

[0191] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

[0192]3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,

[0193] 3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

[0194] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0195]4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0196] 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

[0197]8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

[0198] 8-hydroxyquinoline sulphate,

[0199] 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

[0200]bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

[0201] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0202]cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholinehydrochloride,

[0203] ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

[0204] potassium bicarbonate,

[0205] methanetetrathiol-sodium salt,

[0206] methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0207] methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0208] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0209] N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

[0210]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0211]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0212] N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

[0213] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0214] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0215]N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

[0216] N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

[0217] N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

[0218]N-[3-chloro-4,5-bis(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

[0219] N-formyl-N-hydroxy-DL-alanine-sodium salt,

[0220] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0221] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0222] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0223] spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,

[0224] Bactericides:

[0225] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0226] Insecticides/acaricides nematicides:

[0227] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alphacypermethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

[0228]Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

[0229] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfhan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

[0230] deltamethrin, demeton M, demeton S, demeton-S-methyl,diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0231] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., eprinomectin, esfenvalerate, ethiofencarb, ethion, ethoprophos,etofenprox, etoxazole, etrimfos,

[0232] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate, fubfenprox,furathiocarb,

[0233] granulosis viruses,

[0234] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene,

[0235] imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

[0236] nuclear polyhedrosis viruses,

[0237] lambda-cyhalothrin, lufenuron,

[0238] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methomyl, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,milbemectin, milbemycin, monocrotophos,

[0239] naled, nitenpyram, nithiazine, novaluron,

[0240] omethoate, oxamyl, oxydemethon M,

[0241]Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb, propoxur,prothiofos, prothoate, pymetrozine, pyraclofos, pyresmethrin, pyrethrum,pyridaben, pyridathion, pyrimidifen, pyriproxyfen,

[0242] quinalphos,

[0243] ribavirin,

[0244] salithion, sebufos, silafluofen, spinosad, sulphotep, sulprofos,

[0245] tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, theta-cypermethrin, thiamethoxam, thiapronil,thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiofanox,thuringiensin, tralocythrin, tralomethrin, triarathene, triazamate,triazophos, triazuron, trichlophenidine, trichlorfon, triflumuron,trimethacarb,

[0246] vamidothion, vaniliprole, Verticillium lecanii,

[0247] YI 5302,

[0248] zeta-cypermethrin, zolaprofos,

[0249] (1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate,

[0250] (3-phenoxyphenyl)-methyl2,2,3,3-tetramethylcyclopropanecarboxylate,

[0251]1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine,

[0252]2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole,

[0253] 2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione,

[0254]2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0255]2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide,

[0256] 3-methylphenyl propylcarbamate.

[0257] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene,

[0258]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

[0259]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone,

[0260]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone,

[0261]Bacillus thuringiensis strain EG-2348,

[0262] [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid,

[0263]2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate,

[0264][3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide,

[0265] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde,

[0266] ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate,

[0267] N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine,

[0268]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

[0269] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine,

[0270] N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide,

[0271] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide,

[0272] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate

[0273] It is also possible to admix other known active compounds, suchas herbicides, fertilizers and growth regulators.

[0274] When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergistic agents. Synergistic agents are compoundswhich increase the action of the active compounds according to theinvention, without it being necessary for the synergistic agent added tobe active itself.

[0275] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0276] The compounds are employed in a customary manner appropriate forthe use forms.

[0277] When used against hygiene pests and pests of stored products, theactive compound is distinguished by an excellent residual action on woodand clay as well as a good stability to alkali on limed substrates.

[0278] As already mentioned above, it is possible to treat all plantsand their parts according to the invention. In a preferred embodiment,wild plant species and plant cultivars, or those obtained byconventional biological breeding, such as crossing or protoplast fusion,and parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

[0279] Particularly preferably, plants of the plant cultivars which arein each case commercially available or in use are treated according tothe invention. Plant cultivars are to be understood as meaning plantshaving specific properties (“traits”) which can be obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.This can be varieties, bio- and genotypes.

[0280] Depending on the plant species or plant cultivars, their locationand growth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

[0281] The preferred transgenic plants or plant cultivars (i.e. thoseobtained by genetic engineering) which are to be treated according tothe invention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapevines), and particular emphasis isgiven to maize, soya beans, potatoes, cotton and oilseed rape. Traitsthat are emphasized are in particular increased defence of the plantsagainst insects by toxins formed in the plants, in particular thoseformed by the genetic material from Bacillus thuringiensis (for example,by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2,Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits that are alsoparticularly emphasized are the increased defence of plants againstfungi, bacteria and viruses by systemic acquired resistance (SAR),systemin, phytoalexihs, elicitovs and resistance genes andcorrespondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample, the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for example,maize, cotton, soya beans), KnockOut® (for example, maize), StarLink®(for example, maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample, maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for example,maize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example, maize). Of course, thesestatements also apply to plant cultivars having these or still to bedeveloped genetic traits, which plants will be developed and/or marketedin the future.

[0282] The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or the mixturesspecifically mentioned in the present text.

[0283] The active compounds according to the invention act not onlyagainst plant, hygiene and stored product pests, but also in theveterinary medicine sector against animal parasites (ectoparasites),such as hard ticks, soft ticks, mange mites, leaf mites, flies (bitingand licking), parasitic fly larvae, lice, hair lice, feather lice andfleas. These parasites include:

[0284] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

[0285] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

[0286] From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

[0287] From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp. From theorder of the Heteropterida, for example, Cimex spp., Triatoma spp.,Rhodnius spp. and Panstrongylus spp. From the order of the Blattarida,for example, Blatta orientalis, Periplaneta americana, Blattellagermanica and Supella spp.

[0288] From the subclass of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroaspp.

[0289] From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

[0290] They have, for example, excellent activity against thedevelopment stages of ticks such as, for example, Amblyomma hebraeum,against parasitic flies such as, for example, Lucilia cuprina andagainst flies, such as, for example, Ctenocephalides felis.

[0291] The active compounds of the formula (I) according to theinvention are also suitable for controlling arthropods which infestagricultural productive livestock, such as, for example, cattle, sheep,goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens,turkeys, ducks, geese and bees, other pets, such as, for example, dogs,cats, caged birds and aquarium fish, and also so-called test animals,such as, for example, hamsters, guinea pigs, rats and mice. Bycontrolling these arthropods, cases of death and reductions inproductivity (for meat, milk, wool, hides, eggs, honey etc.) should bediminished, so that more economic and easier animal husbandry ispossible by use of the active compounds according to the invention.

[0292] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of moulded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

[0293] When used for cattle, poultry, pets and the like, the activecompounds of the formula (I) according to the invention can be used asformulations (for example, powders, emulsions, free-flowingcompositions), which comprise the active compounds according to theinvention in an amount of 1 to 80% by weight, directly or after 100 to10 000-fold dilution, or they can be used as a chemical bath.

[0294] It has furthermore been found that the compounds according to theinvention have a strong insecticidal action against insects whichdestroy industrial materials.

[0295] The following insects may be mentioned as examples and aspreferred—but without limitation:

[0296] Beetles, such as

[0297]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

[0298] Hymenopterons, such as

[0299]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerusaugur.

[0300] Termites, such as

[0301]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitermes flavipes, Reticulitermes santonensis,Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevadensis, Coptotermes formosanus.

[0302] Bristletails, such as Lepisma saccharina.

[0303] Industrial materials in the present connection are to beunderstood as meaning non-living materials, such as, preferably,plastics, adhesives, sizes, papers and cards, leather, wood andprocessed wood products and coating compositions.

[0304] Wood and processed wood products are especially preferablymaterials to be protected from insect infestation.

[0305] Wood and processed wood products which can be protected by theagents according to the invention or mixtures comprising these are to beunderstood as meaning, for example:

[0306] building timber, wooden beams, railway sleepers, bridgecomponents, boat jetties, wooden vehicles, boxes, pallets, containers,telegraph poles, wood panelling, wooden window frames and doors,plywood, chipboard, joinery or wooden products which are used quitegenerally in house-building or in building joinery.

[0307] The active compounds according to the invention can be used assuch, in the form of concentrates or in generally customaryformulations, such as powders, granules, solutions, suspensions,emulsions or pastes. The formulations mentioned can be prepared in amanner known per se, for example by mixing the active compoundsaccording to the invention with at least one solvent or diluent,emulsifier, dispersing agent and/or binder or fixing agent, a waterrepellent, if appropriate siccatives and UV stabilizers and, ifappropriate, dyestuffs and pigments, and also other processingauxiliaries.

[0308] The insecticidal compositions or concentrates used for thepreservation of wood and wood-derived timber products comprise theactive compound according to the invention in a concentration of 0.0001to 95% by weight, in particular 0.001 to 60% by weight.

[0309] The amount of the compositions or concentrates employed dependson the nature and occurrence of the insects and on the medium. Theoptimum amount employed can be determined for the use in each case by aseries of tests. In general, however, it is sufficient to employ 0.0001to 20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be preserved.

[0310] Solvents and/or diluents which are used are an organic chemicalsolvent or solvent mixture and/or an oily or oil-like organic chemicalsolvent or solvent mixture of low volatility and/or a polar organicchemical solvent or solvent mixture and/or water, and, if appropriate,an emulsifier and/or wetting agent.

[0311] Organic chemical solvents which are preferably used are oily oroil-like solvents having an evaporation number above 35 and a flashpointabove 30° C., preferably above 45° C. Substances which are used as suchoily or oil-like water-insoluble solvents of low volatility areappropriate mineral oils or aromatic fractions thereof, or solventmixtures containing mineral oils, preferably white spirit, petroleumand/or alkylbenzene.

[0312] Mineral oils having a boiling range from 170 to 220° C., whitespirit having a boiling range from 170 to 220° C., spindle oil having aboiling range from 250 to 350° C., petroleum and aromatics having aboiling range from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

[0313] In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

[0314] The organic oily or oil-like solvents of low volatility whichhave an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., can be replaced in part by organic chemicalsolvents of high or medium volatility, provided that the solvent mixturelikewise has an evaporation number above 35 and a flashpoint above 30°C., preferably above 45° C., and that the insecticide/fungicide mixtureis soluble or emulsifiable in this solvent mixture.

[0315] According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture is replaced by an aliphatic polar organicchemical solvent or solvent mixture. Aliphatic organic chemical solventscontaining hydroxyl and/or ester and/or ether groups, such as, forexample, glycol ethers, esters or the like, are preferably used.

[0316] Organic chemical binders which are used in the context of thepresent invention are the synthetic resins and/or binding drying oilswhich are known per se, are water-dilutable and/or are soluble ordispersible or emulsifiable in the organic chemical solvents employed,in particular binders consisting of or comprising an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenolic resin, hydrocarbon resin, such asindene-coumarone resin, silicone resin, drying vegetable oils and/ordrying oils and/or physically drying binders based on a natural and/orsynthetic resin.

[0317] The synthetic resin used as the binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances can also be used as binders in an amount of up to 10% byweight. Dyestuffs, pigments, water-repelling agents, odour correctantsand inhibitors or anticorrosive agents and the like which are known perse can additionally be employed.

[0318] It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or a drying vegetable oil. Alkydresins having an oil content of more than 45% by weight, preferably 50to 68% by weight, are preferably used according to the invention.

[0319] All or some of the binder mentioned can be replaced by a fixingagent (mixture) or a plasticizer (mixture). These additives are intendedto prevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

[0320] The plasticizers originate from the chemical classes of phthalicacid esters, such as dibutyl, dioctyl or benzyl butyl phthalate,phosphoric acid esters, such as tributyl phosphate, adipic acid esters,such as di-(2-ethylhexyl) adipate, stearates, such as butyl stearate oramyl stearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulphonicacid esters.

[0321] Fixing agents are based chemically on polyvinyl alkyl ethers,such as, for example, polyvinyl methyl ether or ketones, such asbenzophenone or ethylenebenzophenone.

[0322] Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

[0323] Particularly effective preservation of wood is achieved byimpregnation processes on a large industrial scale, for example vacuum,double vacuum or pressure processes.

[0324] The ready-to-use compositions can also comprise otherinsecticides, if appropriate, and also one or more fungicides, ifappropriate.

[0325] Possible additional mixing partners are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an explicit constituent of the presentapplication.

[0326] Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozideand triflumuron, and also fungicides, such as epoxyconazole,hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole,metconazole, imazalil, dichlorfluanid, tolylfluanid,3-iodo-2-propinyl-butyl carbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

[0327] The compounds according to the invention can at the same time beemployed for protecting objects which come into contact with saltwateror brackish water, such as hulls, screens, nets, buildings, moorings andsignalling systems, against fouling.

[0328] Fouling by sessile Oligochaeta, such as Serpulidae, and by shellsand species from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

[0329] Apart from fouling by algae, for example Ectocarpus sp. andCeramium sp., fouling by sessile Entomostraka groups, which come underthe generic term Cirripedia (cirriped crustaceans), is of particularimportance.

[0330] Surprisingly, it has now been found that the compounds accordingto the invention, alone or in combination with other active compounds,have an outstanding antifouling action.

[0331] Using the compounds according to the invention, alone or incombination with other active compounds, allows the use of heavy metalssuch as, for example, in bis(trialkyltin) sulphides, tri-n-butyltinlaurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl(bispyridine)-bismuth chloride, tri-n-butyltin fluoride, manganeseethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zincoxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds to be substantially reduced.

[0332] If appropriate, the ready-to-use antifouling paints canadditionally comprise other active compounds, preferably algicides,fungicides, herbicides, molluscicides, or other antifouling activecompounds.

[0333] Preferably suitable components in combinations with theantifouling compositions according to the invention are:

[0334] algicides such as

[0335] 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

[0336] fungicides such as

[0337] benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as azaconazole, cyproconazole,epoxyconazole, hexaconazole, metconazole, propiconazole andtebuconazole;

[0338] molluscicides such as

[0339] fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarband trimethacarb;

[0340] or conventional antifouling active compounds such as

[0341] 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridine-triphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleimide.

[0342] The antifouling compositions used comprise the active compoundaccording to the invention of the compounds according to the inventionin a concentration of 0.001 to 50% by weight, in particular 0.01 to 20%by weight.

[0343] Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

[0344] Besides the algicidal, fungicidal, molluscicidal active compoundsand insecticidal active compounds according to the invention,antifouling paints comprise, in particular, binders.

[0345] Examples of recognized binders are polyvinyl chloride in asolvent system, chlorinated rubber in a solvent system, acrylic resinsin a solvent system, in particular in an aqueous system, vinylchloride/vinyl acetate copolymer systems in the form of aqueousdispersions or in the form of organic solvent systems,butadiene/styrene/acrylonitrile rubbers, drying oils such as linseedoil, resin esters or modified hardened resins in combination with tar orbitumens, asphalt and epoxy compounds, small amounts of chlorine rubber,chlorinated polypropylene and vinyl resins.

[0346] If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

[0347] The active compounds according to the invention are also suitablefor controlling animal pests, in particular insects, arachnids andmites, which are found in enclosed spaces such as, for example,dwellings, factory halls, offices, vehicle cabins and the like. They canbe employed alone or in combination with other active compounds andauxiliaries in domestic insecticide products for controlling thesepests. They are active against sensitive and resistant species andagainst all development stages. These pests include:

[0348] From the order of the Scorpionidea, for example, Buthusoccitanus.

[0349] From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

[0350] From the order of the Araneae, for example, Aviculariidae,Araneidae.

[0351] From the order of the Opiliones, for example, Pseudoscorpioneschelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

[0352] From the order of the Isopoda, for example, Oniscus asellus,Porcellio scaber.

[0353] From the order of the Diplopoda, for example, Blaniulusguttulatus, Polydesmus spp.

[0354] From the order of the Chilopoda, for example, Geophilus spp.

[0355] From the order of the Zygentoma, for example, Ctenolepisma spp.,Lepisma saccharina, Lepismodes inquilinus.

[0356] From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

[0357] From the order of the Saltatoria, for example, Acheta domesticus.

[0358] From the order of the Dermaptera, for example, Forficulaauricularia.

[0359] From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

[0360] From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

[0361] From the order of the Coleptera, for example, Anthrenus spp.,Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinusspp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

[0362] From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

[0363] From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

[0364] From the order of the Siphonaptera, for example, Ctenocephalidescanis, Ctenocephalides felis, Pulex irritans, Tunga penetrans,Xenopsylla cheopis.

[0365] From the order of the Hymenoptera, for example, Camponotusherculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus,Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

[0366] From the order of the Anoplura, for example, Pediculus humanuscapitis, Pediculus humanus corporis, Phthirus pubis.

[0367] From the order of the Heteroptera, for example, Cimex hemipterus,Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

[0368] In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticides.

[0369] They are used as aerosols, pressure-free spray products, forexample pump and atomizer sprays, automatic fogging systems, foggers,foams, gels, evaporator products with evaporator tablets made ofcellulose or polymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free or passive evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

[0370] The preparation and use of the substances according to theinvention is shown in the examples below.

PREPARATION EXAMPLES Example 1

[0371]

[0372] At 100° C., 0.50 g (1.137 mmol) of4-chloro-2-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-isoindole-1,3(2H)-dioneand 0.222 g (1.251 mmol) of1-{[(trimethylsilyl)methyl]sulphanyl}-2-propanamine are stirred in theabsence of a solvent for 1 h. The crude product is then purified bysilica gel column chromatography (mobile phase: dichloromethane).

[0373] Isomer 1:

3-Chloro-N²-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N¹-(1-methyl-2-{[(trimethylsilyl)methyl]sulphanyl}ethyl)phthalamide

[0374] Yield: 0.12 g (15% of theory) m.p.: 159-160° C. HPLC: log P (pH2.3) = 5.38 ¹H-NMR (CD₃CN): δ = 0 (9H), 1.15 (d, 3H), 1.74 (m, 2H), 2.32(s, 3H), 2.55 (m, 1H), 2.65 (m, 1H), 4.14 (m, 1H), 6.85 (m, 1H), 7.55(m, 5H), 8.05 (m, 1H), 8.30 (m, 1H) ppm.

[0375] Isomer 2:

3-Chloro-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(1-methyl-2-{[(trimethylsilyl)methyl]sulphanyl}ethyl)phthalamide

[0376] Yield: 0.20 g (27% of theory) m.p.: 161-162° C. HPLC log P (pH2.3) = 5.56 ¹H-NMR (CD₃CN): δ = 0 (9H), 1.15 (d, 3H), 1.75 (m, 2H), 2.35(s, 3H), 2.5 (m, 1H), 2.65 (m, 1H), 4.15 (m, 1H), 6.95 (m, 1H), 7.55 (m,3H), 7.65 (m, 1H), 7.75 (m, 1H), 8.15 (m, 1H), 8.55 (m, 1H) ppm.

Example 2

[0377]

[0378] 0.50 g (1.29 mmol) of4-chloro-2-[2-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-isoindole-1,3(2H)-dioneand 0.38 g (3.65 mmol) of trimethylsilylmethylamine are heated at refluxfor 16 h. The reaction mixture is then concentrated under reducedpressure and the crude product is triturated with diisopropyl ether.

[0379] Isomer Mixture

3-Chloro-N¹-[2-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-N²-[(trimethylsilyl)methyl]phthalamide(Isomer 1) and3-chloro-N²-[2-methyl-4-(1,1,2,2tetrafluoroethoxy)phenyl]-N¹-[(trimethylsilyl)methyl]phthalamide(Isomer 2)

[0380] Yield: 0.55 g (56% of theory) HPLC: log P (pH 2.3) = 3.59 and3.69 ¹H-NMR (CD₃CN): δ = 0.1 (9H), 2.25 (s, 3H), 2.75 (s, 2H), 6.12 (m,1H), 6.7-8.5 (m, 8H) ppm.

Example 3

[0381]

[0382] 0.80 g (1.819 mmol) of4-chloro-2-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-isoindole-1,3(2H)-dioneand 0.587 g (3.639 mmol) of2-methyl-2-[(trimethylsilyl)oxy]-1-propanamine are stirred at 100° C. inthe absence of a solvent for 1 h. The crude product is then purified bysilica gel column chromatography (mobile phase: dichloromethane).

[0383] Isomer 1:

3-Chloro-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-{2-methyl-2-[(trimethylsilyl)oxy]propyl}phthalamide

[0384] Yield: 0.42 g (23% of theory) m.p.: 144-145° C. HPLC: log P (pH2.3) = 3.11 ¹H-NMR (CD₃CN): δ = 0 (9H), 1.15 (s, 6H), 2.3 (s, 3H), 3.2(m, 2H), 6.70-8.50 (m, 8H).

[0385] Isomer 2:

3-Chloro-N²-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N¹-{2-methyl-2-[(trimethylsilyl)oxy]propyl}phthalamide

[0386] Yield: 0.27 g (22% of theory) m.p.: 163-164° C. HPLC: log P (pH2.3) = 3.19 ¹H-NMR (CD₃CN): δ = 0 (9H), 1.1 (s, 3H), 1.15 (s, 3H), 2.3(s, 3H), 3.25 (m, 2H), 6.95 (m, 1H), 7.45 (m, 3H), 7.60 (m, 2H), 7.95(m, 1H), 8.35 (m, 1H) ppm.

[0387] The following compounds can be obtained according to one ofExamples 1 to 3:

No. X Y —(CR¹R²)_(a)—A_(b)—(CR³R⁴)_(c)—Si(R⁵R⁶R⁷) log P (pH 2.3) 4 3-Cl2′-Me, 4′-i-C₃F₇ —CH₂SiMe₃ 4.72 5 6-Cl 2′-Me, 4′-i-C₃F₇ —CH₂SiMe₃ 4.58 63-Cl 2′-Me, 4′-OCF₃ —CH₂SiMe₃ 7 6-Cl 2′-Me, 4′-OCF₃ —CH₂SiMe₃ 8 3-Cl2′-Me, 4′-i-C₃F₇ —(CH₂)₃Si(OMe)₃ 9 6-Cl 2′-Me, 4′-i-C₃F₇—(CH₂)₃—Si(OMe)₃ 10 3-Cl 2′-Me, 4′-OCF₃ —(CH₂)₃—Si(OMe)₃ 11 6-Cl 2′-Me,4′-OCF₃ —(CH₂)₃—Si(OMe)₃ 12 3-Cl 2′-Me, 4′-i-C₃F₇—CH(Me)—CH₂—S—CH₂—SiMe(OEt)₂ 13 6-Cl 2′-Me, 4′-i-C₃F₇—CH(Me)—CH₂—S—CH₂—SiMe(OEt)₂ 14 3-Cl 2′-Me, 4′-OCF₃—CH(Me)—CH₂—S—CH₂—SiMe(OEt)₂ 15 6-Cl 2′-Me, 4′-OCF₃—CH(Me)—CH₂—S—CH₂—SiMe(OEt)₂ 16 3-I 2′-Me, 4′-i-C₃F₇—CH(Me)—CH₂—S—CH₂—SiMe₃ 5.69 17 6-I 2′-Me, 4′-i-C₃F₇—CH(Me)—CH₂—S—CH₂—SiMe₃ 5.46 18 3-I 2′-Me, 4′-OCF₃—CH(Me)—CH₂—S—CH₂—SiMe₃ 19 6-I 2′-Me, 4′-OCF₃ —CH(Me)—CH₂—S—CH₂—SiMe₃ 203-I 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—S—CH₂—SiMe₃ 21 6-I 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—S—CH₂—SiMe₃ 22 3-I 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—SO—CH₂—SiMe₃23 6-I 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—SO—CH₂—SiMe₃ 24 3-I 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 25 6-I 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 26 3-Br 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—S—CH₂—SiMe₃ 27 6-Br 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—S—CH₂—SiMe₃28 3-Br 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—SO—CH₂—SiMe₃ 29 6-Br 2′-Me,4′-i-C₃F₇ —C(Me)₂—CH₂—SO—CH₂—SiMe₃ 30 3-Br 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 31 6-Br 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 32 3-Cl 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—S—CH₂—SiMe₃ 33 6-Cl 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—S—CH₂—SiMe₃34 3-Cl 2′-Me, 4′-i-C₃F₇ —C(Me)₂—CH₂—SO—CH₂—SiMe₃ 35 6-Cl 2′-Me,4′-i-C₃F₇ —C(Me)₂—CH₂—SO—CH₂—SiMe₃ 36 3-Cl 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 37 6-Cl 2′-Me, 4′-i-C₃F₇—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 38 3-I

—CH(Me)—CH₂—S—CH₂—SiMe₃ 5.55 39 6-I

—CH(Me)—CH₂—S—CH₂—SiMe₃ 5.39 40 3-Cl

—CH(Me)—CH₂—S—CH₂—SiMe₃ 5.41 41 6-Cl

—CH(Me)—CH₂—S—CH₂—SiMe₃ 5.26 42 3-I

—CH(Me)—CH₂—S—CH₂—SiMe₃ 4.98 43 6-I

—CH(Me)—CH₂—S—CH₂—SiMe₃ 4.70 44 3-I

—CH(Me)—CH₂—S—CH₂—SiMe₃ 45 6-I

—CH(Me)—CH₂—S—CH₂—SiMe₃ 46 3-I

—CH(Me)—CH₂—SO—CH₂—SiMe₃ 47 6-I

—CH(Me)—CH₂—SO—CH₂—SiMe₃ 48 3-I

—CH(Me)—CH₂—SO₂—CH₂—SiMe₃ 49 6-I

—CH(Me)—CH₂—SO₂—CH₂—SiMe₃ 50 3-I

—C(Me)₂—CH₂—S—CH₂—SiMe₃ 51 6-I

—C(Me)₂—CH₂—S—CH₂—SiMe₃ 52 3-I

—C(Me)₂—CH₂—SO—CH₂—SiMe₃ 53 6-I

—C(Me)₂—CH₂—SO—CH₂—SiMe₃ 54 3-I

—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃ 55 6-I

—C(Me)₂—CH₂—SO₂—CH₂—SiMe₃

[0388] Preparation of the Starting Materials:

[0389] 1.66 g (13.8 mmol) of trimethylsilylmethanethiol are initiallycharged at 0° C. in 20 ml of methanol. 0.788 g (13.8 mmol) of2-methylaziridine is added dropwise, the mixture is stirred at 0° C. foranother 4 h and then heated at reflux for 8 h, and the reaction mixtureis subsequently concentrated under reduced pressure. Yield: 1.84 g (48%of theory) of 1-{[(trimethylsilyl)- methyl]sulphanyl}-2-propanamide asan oil HPLC: log P (pH 2.3) = 1.28 ¹H-NMR (CD₃CN): δ = 0.05 (9H), 1.15(d, 3H), 1.75 (q, 2H), 2.50 (m, 2H), 2.85 (br, 2H), 3.10 (m, 1H) ppm.

[0390] The stated logP values were determined in accordance with EECdirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C 18). Temperature: 43°C.

[0391] In the acidic range, the determination was carried out at pH 2.3using the mobile phases 0.1% aqueous phosphoric acid and acetonitrile;linear gradient from 10% acetonitrile to 90% acetonitrile.

[0392] Calibration was carried out using unbranched alkan-2-ones (having3 to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones.

[0393] The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

USE EXAMPLES Example A

[0394]Heliothis virescens Test Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycolether

[0395] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0396] Soybean shoots (Glycine max) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with Heliothis virescens caterpillars while the leaves arestill moist.

[0397] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0398] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE A Plant-damaging insectsHeliothis virescens test Concentration Kill rate of active com- in %Active compounds pound in ppm after 7^(d)

500 100

500 100

500 100

500 100

Example B

[0399] Phaedon Larvae Test Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycolether

[0400] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0401] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with larvae of the mustard beetle (Phaedon cochleariae)while the leaves are still moist.

[0402] After the desired period of time, the kill in % is determined.100% means that all beetle larvae have been killed; 0% means that noneof the beetle larvae have been killed.

[0403] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE B Plant-damaging insectsPhaedon larvae test Concentration of active Kill rate in % Activecompounds compound in ppm after 7^(d)

500 90

500 100

500 100

500 100

500 100

Example C

[0404] Plutella Test, Sensitive Strain Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycolether

[0405] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0406] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the diamond back moth (Plutellaxylostella, sensitive strain) while the leaves are still moist.

[0407] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0408] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE C Plant-damaging insectsPlutella test, sensitive strain Concentration Kill rate of active com-in % Active compounds pound in ppm after 7^(d)

500 100

500 100

500 100

500 100

Example D

[0409] Plutella Test, Resistant Strain Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycolether

[0410] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0411] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the diamond back moth (Plutellaxylostella, resistant strain) while the leaves are still moist.

[0412] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0413] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE D Plant-damaging insectsPlutella test, resistant strain Concentration Kill rate of active com-in % Active compounds pound in ppm after 7^(d)

500 100

500 100

Example E

[0414]Spodoptera exigua Test Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycolether

[0415] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0416] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the army worm (Spodoptera exigua)while the leaves are still moist.

[0417] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0418] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE E Plant-damaging insectsSpodoptera exigua test Concentration Kill rate of active com- in %Active compounds pound in ppm after 7^(d)

500 100

500 100

500 100

500 100

Example F

[0419]Spodoptera frugiperda Test Solvent: 7 parts by weight ofdimethylformamide Emulsifier: 2 parts by weight of alkylaryl polyglycolether

[0420] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted withemulsifier-containing water to the desired concentration.

[0421] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the army worm (Spodoptera frugiperda)while the leaves are still moist.

[0422] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

[0423] In this test, for example, the following compounds of thePreparation Examples show good activity: TABLE F Plant-damaging insectsSpodoptera frugiperda test Concentration of active Kill rate in % Activecompounds compound in ppm after 7^(d)

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

500 100

Example G

[0424]Diabrotica balteata Test (Larvae in Soil)

[0425] Critical Concentration Test/Soil Insects—Treatment of TransgenicPlants Solvent: 7 parts by weight of dimethylformamide Emulsifier: 1part by weight of alkylaryl polyglycol ether

[0426] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0427] The preparation of active compound is poured onto the soil. Here,the concentration of active compound in the preparation is virtuallyimmaterial, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots, and these are allowed to stand at 20° C.

[0428] Immediately after the preparation, 5 pregerminated maize corns ofthe cultivar YIELD GUARD (trademark of Monsanto Comp., USA) are placedinto each pot. After 2 days, the corresponding test insects are placedinto the treated soil. After a further 7 days, the efficacy of theactive compound is determined by counting the number of maize plantsthat have emerged (1 plant=20% activity).

Example H

[0429]Heliothis virescens Test (Treatment of Transgenic Plants) Solvent:7 parts by weight of dimethylformamide Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

[0430] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0431] Soybean shoots (Glycine max) of the cultivar Roundup Ready(trademark of Monsanto Comp. USA) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with the tobacco budworm caterpillar Heliothis virescens whilethe leaves are still moist.

[0432] After the desired period of time, the kill in % is determined.100% means that all caterpillars have been killed; 0% means that none ofthe caterpillars have been killed.

1. Phthalamides of the formula (I)

in which X and Y independently of one another represent hydrogen,halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy,cycloalkyl, halogenocycloalkyl, cycloalkyloxy, halogenocycloalkyloxy,—S(O)_(d)-alkyl, —S(O)_(d)-halogenoalkyl or represent in each caseoptionally substituted phenyl, phenoxy, heteroaryl or heteroaryloxy, nrepresents 1, 2, 3 or 4, m represents 1, 2, 3, 4 or 5, R¹, R², R³ and R⁴independently of one another represent hydrogen, alkyl, halogenoalkyl orcycloalkyl, R⁵, R⁶ and R⁷ independently of one another represent alkylor alkoxy, A represents —S(O)_(d)— or oxygen, a represents 1, 2, 3 or 4,with the proviso that the repeat unit —CR¹R²— may have identical ordifferent meanings if a represents 2, 3 or 4, b represents 0 or 1, crepresents 0, 1, 2, 3 or 4, with the proviso that the repeat unit—CR³R⁴— may have identical or different meanings if c represents 2, 3 or4, d represents 0, 1 or
 2. 2. Phthalamides of the formula (I) accordingto claim 1, in which X and Y independently of one another representhydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl,C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, C₃-C₆-cycloalkyl,C₃-C₆-halogenocycloalkyl, C₃-C₆-cycloalkyloxy,C₃-C₆-halogenocycloalkyloxy, —S(O)_(d)—C₁-C₆-alkyl,—S(O)_(d)—C₁-C₆-halogenoalkyl or represent phenyl, phenoxy, heteroarylor heteroaryloxy, each of which is optionally mono- to tetrasubstitutedby identical or different substituents from the group consisting ofhalogen, C₁-C₆-alkyl and C₁-C₆-halogenoalkyl, X and Y furthermoreindependently of one another represent phenyl, phenoxy, heteroaryl orheteroaryloxy, each of which is optionally mono- to tetrasubstituted byidentical or different substituents from the group consisting ofC₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy, C₁-C₆-alkylthio andC₁-C₆-halogenoalkylthio, n represents 1, 2 or 3, m represents 1, 2, 3 or4, R¹, R², R³ and R⁴ independently of one another represent hydrogen,C₁-C₆-alkyl, C₁-C₆-halogenoalkyl or C₃-C₆-cycloalkyl, R⁵, R⁶ and R⁷independently of one another represent C₁-C₆-alkyl or C₁-C₆-alkoxy, Arepresents —S(O)_(d)— or oxygen, a represents 1, 2, 3 or 4, with theproviso that the repeat unit —CR¹R²— may have identical or differentmeanings if a represents 2, 3 or 4, b represents 0 or 1, c represents 0,1, 2, 3 or 4, with the proviso that the repeat unit —CR³R⁴— may haveidentical or different meanings if c represents 2, 3 or 4, d represents0, 1 or
 2. 3. Phthalamides of the formula (I) according to claim 2, inwhich X and Y independently of one another represent hydrogen, halogen,cyano, nitro, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy,C₁-C₆-halogenoalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-halogenocycloalkyl,C₃-C₆-cycloalkyloxy, C₃-C₆-halogenocycloalkyloxy, —S(O)_(d)—C₁-C₆-alkyl,—S(O)_(d)—C₁-C₆-halogenoalkyl or represent phenyl, phenoxy, heteroarylor heteroaryloxy, each of which is mono- to tetrasubstituted byidentical or different substituents from the group consisting ofhalogen, C₁-C₆-alkyl, C₁-C₆-halogenoalkyl, and n, m, R¹, R², R³, R⁴, R⁵,R⁶, R⁷, A, a, b, c and d have the meanings given in claim
 2. 4.Phthalamides of the formula (I) according to claim 1, in which X and Yindependently of one another represent hydrogen, fluorine, chlorine,bromine, iodine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1to 9 fluorine, chlorine and/or bromine atoms, C₁-C₄-alkoxy,C₁-C₄-halogenoalkoxy having 1 to 9 fluorine, chlorine and/or bromineatoms, C₃-C₆-cycloalkyl, —S(O)_(d)—C₁-C₄-alkyl,—S(O)_(d)—C₁-C₄-halogenoalkyl having 1 to 9 fluorine, chlorine and/orbromine atoms, Y furthermore represents phenyl, phenoxy, 5- or6-membered heteroaryl or heteroaryloxy having 1 to 4 heteroatomsincluding 0 to 4 nitrogen atoms, 0 to 2 nonadjacent oxygen atoms and/or0 to 2 nonadjacent sulphur atoms (in particular furyl, furyloxy,thienyl, thienyloxy, pyrrolyl, pyrrolyloxy, tetrazolyl, pyridyl,pyridyloxy, pyrimidinyl, pyrimidinyloxy, pyridazinyl, pyridazinyloxy,pyrazinyl, pyrazinyloxy), each of which is optionally mono- totetrasubstituted by identical or different substituents from the groupconsisting of fluorine, chlorine, bromine, iodine, C₁-C₄-alkyl,C₁-C₄-halogenoalkyl having 1 to 9 fluorine, chlorine and/or bromineatoms, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 9 fluorine,chlorine and/or bromine atoms, C₁-C₄-alkylthio, C₁-C₄-halogenoalkylthiohaving 1 to 9 fluorine, chlorine and/or bromine atoms, n represents 1 or2, m represents 1, 2 or 3, R¹, R², R³ and R⁴ independently of oneanother represent hydrogen, C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to9 fluorine, chlorine and/or bromine atoms or C₃-C₆-cycloalkyl, R⁵, R⁶and R⁷ independently of one another represent C₁-C₃-alkyl orC₁-C₃-alkoxy, A represents —S(O)_(d)— or oxygen, a represents 1, 2 or 3,with the proviso that the repeat unit —CR¹R²— may have identical ordifferent meanings if a represents 2 or 3, b represents 0 or 1, crepresents 0, 1, 2 or 3, with the proviso that the repeat unit —CR³R⁴—may have identical or different meanings if c represents 2 or 3, drepresents 0, 1 or
 2. 5. Phthalamides of the formula (I) according toclaim 4, in which X and Y independently of one another representhydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro,C₁-C₄-alkyl, C₁-C₄-halogenoalkyl having 1 to 9 fluorine, chlorine and/orbromine atoms, C₁-C₄-alkoxy, C₁-C₄-halogenoalkoxy having 1 to 9fluorine, chlorine and/or bromine atoms, C₃-C₆-cycloalkyl,—S(O)_(d)—C₁-C₄-alkyl, —S(O)_(d)—C₁-C₄-halogenoalkyl having 1 to 9fluorine, chlorine and/or bromine atoms, and n, m, R¹, R², R³, R⁴, R⁵,R⁶, R⁷, A, a, b, c and d having the meanings given in claim
 4. 6.Phthalamides of the formula (I) according to claim 1, in which Xrepresents chlorine, bromine, iodine, Y represents methyl, ethyl,n-propyl, isopropyl, trifluoromethyl, pentafluoroethyl,n-heptafluoropropyl, isoheptafluoropropyl, trifluoromethoxy or—OCF₂CF₂H, Y furthermore represents phenoxy, pyridinyloxy or tetrazolyl,each of which is mono- to trisubstituted by identical or differentsubstituents from the group consisting of fluorine, chlorine, bromine,iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, —CF₃, —CHF₂, —CClF₂, —CF₂CHFCl, —CF₂CH₂F,—CF₂CCl₃, —CH₂CF₃, —CF₂CHFCF₃, —CH₂CF₂H, —CH₂CF₂CF₃, —CF₂CF₂H,—CF₂CHFCF₃, —OCF₃, —OCHF₂, —OCF₂CF₂H, —SCF₃, —SCHF₂, n represents 1, mrepresents 2, R¹, R², R³ and R⁴ independently of one another representhydrogen, methyl or ethyl, R⁵, R⁶ and R⁷ independently of one anotherrepresent methyl, ethyl, methoxy or ethoxy, A represents —S(O)_(d)— oroxygen, a represents 1, 2 or 3, with the proviso that the repeat unit—CR¹R²— may have identical or different meanings if a represents 2 or 3,b represents 0 or 1, c represents 0, 1 or 2, with the proviso that therepeat unit —CR³R⁴— may have identical or different meanings if crepresents 2, d represents 0, 1 or
 2. 7. Phthalamides of the formula (I)according to claim 6, in which Y represents methyl, ethyl, n-propyl,isopropyl, trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl,isoheptafluoropropyl, trifluoromethoxy or —OCF₂CF₂H, and X, n, m, R¹,R², R³, R⁴, R⁵, R⁶, R⁷, A, a, b, c and d have the meanings given inclaim
 6. 8. Phthalamides of the formula (I-a)

in which Y¹ and Y² independently of one another represent hydrogen,halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy,cycloalkyl, halogenocycloalkyl, cycloalkyloxy, halogenocycloalkyloxy,—S(O)_(d)-alkyl, —S(O)_(d)-halogenoalkyl or represent in each caseoptionally substituted phenyl, phenoxy, heteroaryl or heteroaryloxy, Arepresents sulphur or oxygen, b represents 0 or 1, X, R¹, R², R³, R⁴,R⁵, R⁶, R⁷, a and c have the meanings given in one of claims 1 to
 7. 9.Phthalamides of the formula (I-b)

in which Y¹ and Y² independently of one another represent hydrogen,halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy,cycloalkyl, halogenocycloalkyl, cycloalkyloxy, halogenocycloalkyloxy,—S(O)_(d)-alkyl, —S(O)_(d)-halogenoalkyl or represent in each caseoptionally substituted phenyl, phenoxy, heteroaryl or heteroaryloxy, Arepresents sulphur or oxygen, b represents 0 or 1 and X, R¹, R², R³, R⁴,R⁵, R⁶, R⁷, a and c have the meanings given in one of claims 1 to
 7. 10.Phthalamides of the formula (I-a) according to claim 8, in which Arepresents SO or SO₂.
 11. Phthalamides of the formula the formula (I-b)according to claim 9, in which A represents SO or SO₂.
 12. Phthalamidesof the formula (I-a) according to claim 8, in which Y¹ representsC₁-C₄-alkyl, preferably trifluoromethyl, pentafluoroethyl,n-heptafluoropropyl, isoheptafluoropropyl, particularly preferablyisoheptafluoropropyl.
 13. Phthalamides of the formula the formula (I-b)according to claim 9, in which Y¹ represents C₁-C₄-alkyl, preferablytrifluoromethyl, pentafluoroethyl, n-heptafluoropropyl,isoheptafluoropropyl, particularly preferably isoheptafluoropropyl. 14.Phthalamides of the formula (I-a) according to claim 8, in which Y²represents methyl.
 15. Phthalamides of the formula the formula (I-b)according to claim 9, in which Y² represents methyl.
 16. Phthalamides ofthe formula (I) according to any of claims 1 to 7, in which R⁵, R⁶ andR⁷ each represent methyl.
 17. Phthalamides of the formula (I) accordingto any of claims 1 to 7, in which A represents S, SO or SO₂. 18.Phthalamides of the formula (I) according to claim 1, selected from thegroup consisting of3-chloro-N²-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N¹-(1-methyl-2-{[(trimethylsilyl)methyl]sulphanyl}ethyl)phthalamide,3-chloro-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-(1-methyl-2-{[(trimethylsilyl)methyl]sulphanyl}ethyl)phthalamide,3-chloro-N¹-[2-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-N²-[(trimethylsilyl)methyl]phthalamide,3-chloro-N²-[2-methyl-4-(1,1,2,2-tetrafluoroethoxy)phenyl]-N¹-[(trimethylsilyl)methyl]phthalamide,3-chloro-N¹-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N²-{2-methyl-2-[(trimethylsilyl)oxy]propyl}phthalamide,3-chloro-N²-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N¹-{2-methyl-2-[(trimethylsilyl)oxy]propyl}phthalamide.19. Process for preparing compounds of the formula (I) according toclaim 1 or 2, characterized in that imides of the formula (II)

 in which X, Y, n and m have the meanings given in claim 1 or 2  arereacted with silylamines of the formula (III)H₂N—(CR¹R²)_(a)-A_(b)-(CR³R⁴)_(c)—Si(R⁵R⁶R⁷)  (III)  in which R¹, R²,R³, R⁴, R⁵, R⁶, R⁷, A, a, b and c have the meanings given in claim 1 or2,  if appropriate in the presence of a diluent.
 20. Pesticides,characterized in that they comprise at least one compound of the formula(I) according to claim 1 or 2, in addition to extenders and/orsurfactants.
 21. Use of compounds of the formula (I) according to claim1 or 2 for controlling pests.
 22. Method for controlling pests,characterized in that compounds of the formula (I) according to claim 1or 2 are allowed to act on pests and/or their habitat.
 23. Process forpreparing pesticides, characterized in that compounds of the formula (I)according to claim 1 or 2 are mixed with extenders and/or surfactants.